“I’ll take the Macallan, 18-year,” he said. The Scotch, which costs $26 a glass, appeared before him on a napkin.

“You’re living the dream,” I told him.

He smiled sheepishly. His lifestyle is what thugs in his old neighborhood rap about. He owns a couple of condos; vacations in Miami and Vegas. Once a year, he buys an expensive cigar.

He likes to say he’s “from the projects,” but not “of” the projects.

“Every Friday, my mother would take me to get books from the library,” he said. “I knew it was different compared to my friends. Kids would knock on the door at 9 a.m. and ask if I could come out and play. My mother was like, ‘No, he can’t come out and play.’ Everyone was scared of my mother.”

I haven’t seen this man, whose friends call him D, since he was a 16-year-old junior counselor at a summer camp that I helped run in the Mission Hill public housing development. But I’d heard about his success; his graduation from Boston University; his job at State Street bank. Two decades later, I looked him up to ask what impact the camp had on him.

“I never thought I was that bright of a person,” he said. “But I liked to know things. Talking to you and the other counselors felt like kindred spirits. It made me aware that people who have a good life have a responsibility for others.”

But the longer he spoke, the more I saw the bigger picture of his life, in which we had only played a tiny part. The recurring theme, instead, was his mother’s relentlessness: She warned that his friends’ mistakes could rub off on him. Sure enough, boys he grew up with went off to prison, one by one. His mother, who never finished college, called him during his junior year at BU and insisted he get his master’s degree.

“I looked at the phone like she was crazy,” he said. But he did it.

In fact, most of our former junior counselors seem to have done well. Many were motivated individuals who probably would have succeeded anyway. But we were a force multiplier, offering a paying summer job, a leadership experience, and college role models, all at once. Our junior counselors have gone on to work at the Urban League, Sociedad Latina, Mayor Walsh’s Office of New Bostonians. They’re “jujitsu” jobs that turned the disadvantages of growing up in Mission Hill into strengths.

As D nursed his Scotch, we traded news about the kids we’d worked with. I’d kept in touch with some of them for years. I’d even gone out of my way to help one get a fellowship to work with me in Africa. But she cashed the check and never showed up.

“Any idea where she is now?” I asked.

“Could be dangerous,” he laughed, “to go back and find out what happened to everyone.”

The only kid from our camp I’ve found who’s done as well as D is Tameka Moss, another former junior counselor who still happens to be his very close friend. She graduated from Yale. Today, she’s a business consultant with Next Street, a firm that helps urban entrepreneurs, where she launched a practice that brings in $3 million a year.

The two of them share something almost sacred in common: the journey from the bottom fifth of the socioeconomic ladder to the top fifth. Just 4 percent of the poor manage to make that climb. They are nomads of sorts. They didn’t feel a sense of belonging in the projects, nor do they fit in completely in the white-collar world.

“You have to be comfortable being different,” D said. “Otherwise, it will eat at you.”

About 70 percent of people born poor in America never even make it to the middle class. The journey is so difficult that even those who are given a boost often fail. In the 1990s, the federal government gave vouchers to thousands of randomly selected families in public housing to see how living in wealthier neighborhoods would impact them. Only about half actually used them. In Boston, about a third of those who did move to upscale neighborhoods with the vouchers returned to places of moderate or high poverty within 10 years.

It’s hard to leave everything you know and never look back. It’s so hard that no one but the poor is expected to do it.

D’s mother got a job in a bank and moved to Florida when he was 13. He came back to Mission Hill every summer to live with his grandmother and work at our camp.

He got into Dartmouth, but chose Boston University, where he felt more comfortable. His classmates didn’t treat him differently, but sometimes that almost felt worse.

“They’d think I had a nice bourgie life, like they did,” he said. “Even if I told them I grew up in Mission Hill, they wouldn’t be able to conceptualize it.”

Tameka was also 13 when her family got out. Her mother grew up in the housing development, and was just 17 when Tameka was born. But her parents got married and worked hard. Her father, as a restaurant sous chef. Her mother, in the billing department at Brigham and Women’s Hospital.

It was hard to save enough to move. Thirty percent of their income went to rent. The more they made, the more they paid. By the time they left, their unit in Mission Hill cost the same as their market-rate house in Milford.

But Milford turned out to be a mistake. They discovered its hidden costs: the commute, the loss of free child care at grandma’s, the social isolation of being the only black family.

“They hadn’t thought through what it meant to leave everybody they knew,” Tameka said.

But the biggest problem was the fact that Tameka’s place at Boston Latin had been secured on the condition that she live inside the city. After the move, a jealous acquaintance in Mission Hill called the school. Tameka risked getting kicked out.

Luckily, she was a stellar student. No one wanted her to leave. The school said it would allow her parents to transfer guardianship to her grandmother, who still lived in Mission Hill. In the two-steps-forward-one-step-back journey out of public housing, Tameka was supposed to return to the projects to get the education that would help her escape. In the end, her parents moved back to the city, to Jamaica Plain.

Today, she works with Next Street. She talks passionately about “the guilt that comes from having gotten out,” and “the sadness of all those who could have come with us.”

It’s tempting to see Tameka and D as proof that the American dream is alive and well, that anyone smart and hardworking can make it. But it’s striking how much they had in common that others lacked: Families that sat down together for dinner. Devoted grandparents, aunts and uncles nearby. Father figures. Mothers who set expectations high.

Getting out of poverty is a family affair. Ironically, all that love and support launched them into a socioeconomic strata that values career above all else. Demanding jobs make family life a challenge for Tameka and D. Unlike their peers, neither has children yet.

“You know, you’re never going to find another woman like Tameka,” I said.